Check with Code Enforcement Officer
Have you talked with your town's Code Enforcement Officer? If not, I suggest that you go in-person and ask for his/her suggestions about the overall process. I think they like to be included early, and might be more accommodating if a gray area comes up later. I think it's best to do this as the homeowner, rather than only having your contractor do it.
When I did this a few years ago, I discovered that my contractor didn't quite know all the details for my town so my time at the Town Hall was well spent.
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